Herein is proposed an investigation of chemistry directed toward the ultimate synthesis of the aneoplastic agents, aplysistatin (I), bruceantin (II), and cyclo-(streptolutyl-streptolutyl) (III). One of these active compounds is currently undergoing clinical evaluation and a second is being tested for toxicity in preparation for the same. The proposed syntheses are intended to be of sufficient generality to allow for the preparation of interesting analogs as well as the natural materials themselves and to generate new chemistry for future applications to other synthesis of bioactive molecules. The research will take the following generalized approaches: I. Aplysistatin - the key in this synthesis is a biomimetic brominative cyclization followed by elaboration to the unsaturated lactone. II. Bruceantin - this synthesis addresses the problems created by the extremely heavily oxygenated and stereochemically endowed portion of this complex molecule. III. cyclo-(Streptolutyl-streptolutyl) - the intramolecclar cycloaddition of azides with dipoloraphiles followed by reduction of the resulting nitrogen-containing heterocycles to diamines is the focal point of this synthesis.